Fluoroalkoxy amino triazines for control of weeds in sugar beets

ABSTRACT

This invention comprises novel fluoroalkoxy amino triazines, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides or plant growth regulants.

RELATED APPLICATION

This application is a continuation-in-part of my copending applicationU.S. Pat. application Ser. No. 07/172,593, filed Mar. 24, 1988 nowabandoned.

BACKGROUND OF THE INVENTION

U.S. Pat. No. 4,744,816, issued May 17, 1988, and EP-A-164,269,published on Dec. 11, 1985, disclose herbicidal sulfonylureas of theformula ##STR1## wherein R₁ is, inter alia, CO₂ R₁₀, etc.;

R₂ is H, F, Cl, Br, CF₃, CH₃, C₂ H₅, OCH₃, OC₂ H₅, SCH₃ or SC₂ H₅ ;

R₁₀ is C₁ -C₄ alkyl, CH₂ CH₂ OCH3, CH₂ CH₂ Cl, CH₂ CH═CH₂ or CH₂C.tbd.CH;

R₁₄ is H or C₁ -C₂ alkyl;

R₁₅ is C₁ -C₂ alkyl, OCH₃, OC₂ H₅ or CH₂ CN;

X is NR₁₄ R₁₅ ;

Y is OCH₂ CH₂ F, OCH₂ CHF₂ or OCH₂ CF₃ ; and

Z is CH or N.

South African Application No. 84/2245, published 9/28/84, disclosesherbicidal sulfonylureas of the formula ##STR2## wherein A is C₁ -C₆haloalkyl

Z is O or S;

E is CH or N;

R₁ is, inter alia. H, COR₆, etc.;

R₂ is, inter alia, H, etc.;

R₃ and R₄ are independently H, halogen, C₁ -C₄ alkyl, C₂ -C₄ haloalkoxy,NR₁₂ R₁₃, etc.;

R₆ is, inter alia, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₂ -C₆alkoxyalkoxy, etc.; and

R₁₂ and R₁₃ are independently H or C₁ -C₄ alkyl.

While these two references generically disclose some of the compounds ofthe instant invention, there is no specific mention of the instantcompounds or their utility in sugar beets.

U.S Pat. No. 4,618,363 discloses herbicidal sulfonylureas of the formula##STR3## wherein R₁ is H, halogen, NO₂, C₁ -C₄ haloalkyl, C₁ -C₄ alkyl,C₁ -C₄ alkoxy, C₂ -C₅ alkenyl or C₁ --C₄ alkoxycarbonyl;

X is O, S, --SO-- or SO₂ ;

m is 0 or 1;

Q is, inter alia, R₁₃, etc.;

R₁₃ is phenyl or phenyl substituted by halogen, NO₂, CN, C₁ -C₄ alkyl,C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₂ -C₅ alkenyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxycarbonyl, --NR₄₅ R₄₆, --SO₃ H or --SO2NR₄₇ R₄₈ ;

R₂ is C₁ -C₃ alkyl or C₁ -C₃ alkoxy, each unsubstituted by 1 to 3halogen atoms;

R₃ is, inter alia, --NR₄ R₅, etc.; and

E is N or CH.

While this reference generically discloses some of the compounds of theinstant invention, there is no specific mention of the instant compoundsor their utility in sugar beets.

SUMMARY OF THE INVENTION

This invention comprises novel compounds of Formula I, agriculturallysuitable compositions containing them, and their method-of-use aspreemergence and/or postemergence herbicides or plant growth regulants.##STR4## wherein R is C₁ -C₄ alkyl, CH₂ CH═CH₂, CH₂ C.tbd.CH,cyclopropylmethyl or CH₂ CH₂ R₂ ;

R₁ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, CH₂ CN, CH₂ CH₃, C₁ -C₃ alkoxy, C₁-C₃ alkylthio, phenylthio or NR₃ R₄ ;

R₂ is C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, CN or halogen;

R₃ and R₄ are independently H or CH₃ ; and

X is NHCH₃, N(CH₃)2 or N(CH₃)OCH₃ ; provided that when R₁ is OCH₂ CH₃ orCH₂ OCH₃, then R is other than CH₃ ;

and their agriculturally suitable salts.

In the above definitions, the term "alkyl" includes straight chain orbranched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or thedifferent butyl isomers.

Alkoxy includes methoxy and ethoxy.

Alkylthio includes methylthio and ethylthio.

The term "halogen," either alone or in compound words such as"haloalkyl," means fluorine, chlorine, bromine or iodine. Further, whenused in compound words such as "haloalkyl" said alkyl may be partiallyor fully substituted with halogen atoms, which may be the same ordifferent. Examples of haloalkyl include CF₃, CH₂ CH₂ F, CF₂ CF₃ and CH₂CHFCl.

The total number of carbon atoms in a substituent group is indicated bythe C_(i) -C_(j) prefix where i and j are numbers from 1 to 4. Forexample, C₁ -C₄ alkyl would designate methyl, ethyl and the differentpropyl and butyl isomers; C₁ -C₂ alkylthio would designate methylthioand ethylthio; C₁ -C₂ alkoxy would designate methoxy and ethoxy.

Preferred for reasons of their higher herbicidal activity, greatersafety to sugar beets and/or more favorable ease of synthesis are:

1. Compounds of Formula I wherein

R is C₁ -C₄ alkyl;

R₁ is C₁ -C₂ alkyl; and

X is NHCH₃ or N(CH₃)₂.

2. Compounds of Formula I wherein

R is C₁ -C₄ alkyl;

R₁ is C₁ -C₂ haloalkyl; and

X is NHCH₃ or N(CH₃)₂.

3. Compounds of Preferred 1 wherein

R is C₁ -C₃ alkyl; and

X is NHCH₃.

4. Compounds of Preferred 1 wherein

R is C₁ -C₃ alkyl; and

X is N(CH₃)₂.

Specifically preferred for reasons of highest herbicidal activity,greatest safety to sugar beets and/or most favorable ease of synthesisare:

Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate,melting point 134-142° C.; and

Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethyoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate,melting point 150-160° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The following discussion represents a general outline for thepreparation of the compounds of this invention. All of the synthesesdescribed below are multistep with one or more methods being taught foreach step. This allows for a wide variety of possible synthetic pathwaysto prepare a particular compound of Formula I. The proper choice of thesynthetic pathway and the best ordering of the reaction sequences foreach individual will be known to one skilled in the art.

The compounds of Formula I can be prepared by the methods shown inEquations 1 and 2.

As shown in Equation 1, many of the compounds of Formula I can beprepared by reacting a silyl sulfonamide of Formula II with aheterocyclic carbamate of Formula III. ##STR5##

The reaction is carried out at 0° to 50° C. in a solvent such asacetonitrile, dioxane, or tetrahydrofuran in the presence of a fluorideion source such as cesium fluoride or tetrabutylammonium fluoride for0.1 to 2 hours.

Alternatively, some of the sulfonamides of Formula IV can be preparedand reacted with heterocyclic carbamates of Formula III to givecompounds of Formula I as shown in Equation 2. ##STR6##

The reaction is carried out at 0° to 50° C. in a solvent such asacetonitrile, dioxane, or tetrahydrofuran in the presence of anon-nucleophilic base such as DBU for 0.2 to 2 hours.

Many of the silyl sulfonamides of Formula II can be prepared by reactingsulfonyl chlorides of Formula V with t-butyldimethylsilylamine (J. R.Bowser, et al., Inorganic Chemistry. 17. 1882 (1978)) as shown inEquation 3. ##STR7##

The reaction is carried out at 0° to 30° C. in a solvent such asdichloromethane in the presence of 1 to 2 equivalents of the amine and 1equivalent of sodium bicarbonate.

Alternatively, many silyl sulfonamides of Formula II can be prepared byreacting silylsulfonamides of Formula VI with alkyl chloroformates asshown in Equation 4. ##STR8##

The reaction is carried out by contacting suitable silyl sulfonamides ofFormula VI with an organolithium reagent such as n-butyllithium in aninert aprotic solvent such as tetrahydrofuran at -78° to 0° C. for 0.5to 3 hours. The dilithio-intermediate VIa is then reacted with an alkylorthoformate at -78° to 0° C. for 0.5 to 5 hours. Silylsulfonamides IIare isolated by standard methods which are well known to one skilled inthe art.

Many silyl sulfonamides of Formula II can be prepared by the indirectroute shown in Equation 5. ##STR9##

The first two steps are done as described above for Equation 4. J. G.Lombardino (J. Org. Chem., 36, 1843 (1971)) also describes methods forpreparing acid intermediate which are similar to acids of Formula VII.Methods to esterify acids under mild conditions are well known in theart.

Many sulfonamides of Formula IV can be prepared by deprotectingt-butylsulfonamides of Formula IIa as in Equation 6. ##STR10##

The reaction is carried out at -78° to 30° C. in an inert solvent suchas hexane in the presence of an acid such as trifluoroacetic acid. Thesuccess of this reaction depends on the nature of R₁ and R and will beknown to one skilled in the art.

Sulfonamides of Formula IIa can be prepared by methods similar to thosedescribed in Equations 3, 4 and 5 in which the t-butyldimethylsilylmoiety has been replaced by the t-butyl moiety.

The sulfonyl chlorides of Formula V can be prepared by oxidativelychlorinating the corresponding sulfur-containing compounds of FormulaVIII as shown in Equation 7. R ' is H, alkyl, benzyl or carbamoyl.##STR11##

The reaction of Equation 7 is carried out by contacting compounds ofFormula VIII in a solvent such as acetic acid or proprionic acid with atleast 3.0 equivalents of chlorine in the presence of at least 2.5equivalents of water at about -20° to 30° C. for 0.2 to 5 hours. A.Wagenaar teaches specific reaction conditions for related compounds inRecl. Trav. Chim. Pays-Bas 101, 91 (1982).

Alternatively, reaction of compounds of Formula VIII, wherein R' is H orbenzyl, with a hypochlorite solution such as 5% NaOCl can providesulfonyl chlorides of Formula V. Reaction conditions for similarreactions are described in South African Patent Application No. 84/8845and EP-A-142,152.

As shown in Equation 8, many of the sulfonyl chlorides of Formula V canbe prepared from the corresponding amines of Formula IX by a Meerweinreaction. ##STR12##

The reaction involves diazotization of the amine IX with sodium nitritein aqueous HCl, followed by reaction of the diazonium salt with sulfurdioxide and cupric chloride in acetic acid analogous to the teachings ofYale and Sowinski, J. Org.. Chem., 25, 1824 (1960).

Alternatively, sulfonyl chlorides of Formula V can be prepared by amodification of the above procedure as shown in Equation 9. ##STR13##

The amine hydrochloride salts IXa are diazotized with an alkyl nitritein an organic solvent, such as acetonitrile or acetone, and theresulting diazonium salts are reacted with sulfur dioxide and cupricchloride to give sulfonyl chlorides. V. M. Doyle, in J. Org. Chem., 42.2426, 2431 (1977), describes conditions for doing similar Meerweinreactions.

The heterocyclic carbamates of Formula III in Equations 1 and 2 can beprepared by methods described in U.S. Pat. No. 4,744,816.

The preparation of compounds of this invention is further illustrated bythe following examples.

EXAMPLE 1 3-Methyl-2-(phenylmethylthio)-benzoic acid, 1-methylethylester

To a stirred suspension of dry tetrahydrofuran (125mL) and 35% potassiumhydride in oil (6.3 g) was slowly added benzyl mercaptan (6.1 mL) at 0°C. under an inert atmosphere. After 15 minutes, 3-methyl-2-nitrobenzoicacid, 1-methylethyl ester (11.23 g) was added and the resulting mixturewas stirred at room temperature overnight. The reaction mixture waspartitioned between 6N sodium hydroxide (25 mL) and ethyl acetate (150mL). The organic phase was dried over magnesium sulfate, filtered,concentrated, and chromatographed on silica gel eluted with 5% ethylacetate in hexanes to give 13.7 g of the title compound as a yellow oil,n_(D) 1.5642.

90 MHz NMR (CDCl₃): δ 1 39 (d, 6H, CH₃); 2.39 (s, 3H, CH₃); 3.99 (s, 2H,CH₂); 5.32 (m, 1H, CH); and 7.26 (m, 8H, arom.).

IR (neat) 1720 cm⁻¹ .

EXAMPLE 2 Methyl 2-(chlorosulfonyl)-3-methylbenzoate

To a stirred suspension of methyl 3-methyl-2-(Phenylmethylthio)-benzoate(24 g), dichloromethane (700 mL), water (150 mL), and concentratedhydrochloric acid (34 mL), kept at 0° C., was slowly added 5% sodiumhypochlorite (450 mL). The resulting yellow suspension was stirred at 0°C. for 1 hour. The dichloromethane phase was dried over magnesiumsulfate, filtered, concentrated, and triturated withchlorobutane-hexanes to give 14 g of the title compound as a whitesolid, m.p. 114-116° C.

90 MHz NMR (CDCl₃): δ 2.82 (s, 3H, CH₃); 3.97 (s, 3H, OCH₃); and 7.5 (m,3H, arom.).

IR (nujol) 1730, 1360, and 1175 cm⁻¹.

EXAMPLE 3 Ethyl2-[((dimethyl)-(1.1-dimethylethyl)silylamino)sulfonyl]-3-nitrobenzoate

A suspension of ethyl 2-(chlorosulfonyl)-3-nitrobenzoate (14.7 g),amino-t-butyldimethylsilane (15.4 g), and sodium bicarbonate (3.5 g) indichloromethane (300 mL) was stirred at room temperature in a stopperedflask for 4 days. Water (90 mL) and saturated aqueous bicarbonate (45mL) were added, and the mixture was stirred. The dichloromethane phasewas dried over magnesium sulfate, filtered, concentrated, andchromatographed on silica gel eluted with 20% ethyl acetate in hexanesto give 12.9 g of the title compound as a white solid, m.p. 101-102° C.

90 MHz NMR (CDCl₃): δ 0.30 (s, 6H, SiCH₃); 0.97 (s, 9H, CH₃); 1.41 (t,3H, CH₃); 4.48 (q, 2H, OCH₂); 5.86 (s, 1H, NH); and 7.7 (m, 3H, arom.).

IR (nujol) 3200, 1730 and 1700 cm⁻¹.

EXAMPLE 4 Methyl2-[((dimethyl)-1,1-dimethylethyl)silylamino)sulfonyl]-3-trifluoromethylbenzoate

A solution ofN-[(dimethyl)-(1,1-dimethylethyl)silyl]-2-trifluoromethylbenzenesulfonamide(17.5 g) in dry tetrahydrofuran (250 mL) was contacted with 2.5 Mbutyllithium (46 mL) at 50° C. and allowed to warm to 0° C. over 1.5hours under an inert atmosphere. The mixture was cooled to -78° C. andadded to a solution of methyl chloroformate in dry tetrahydrofuran (300mL) at -78° C. The mixture was stirred at -78° C. under an inertatmosphere for 1.5 hours and then quenched with saturated aqueousammonium chloride (100 mL). After warming to 0° C., the tetrahydrofuranlayer was dried over magnesium sulfate, filtered, evaporated, andchromatographed on silica gel eluted with 20% chlorobutane, 10%tetrahydrofuran and 70% hexanes to give 2.13 g of the title compound asa white solid, m.p. 80-84° C.

MHz NMR (CDCl₃): δ0.29 (s, 6H, SiCH₃); 0.96 (s, 9H, CH₃); 4.02 (s, 3H,OCH₃); 5.63 (s, 1H, NH); 7.8 (m, 2H, arom.); and 8 (m, 1H, arom.).

IR (nujol) 3250, 1725 cm⁻¹

EXAMPLE 5 Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate

A solution of2-(dimethyl-(1,1-dimethylethyl)-silylamino)-3-methylbenzoic acid, ethylester (0.36 g) and0-phenyl-N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamate(0.39 g) in acetonitrile (10 mL) was treated with 1M tetrabutylammoniumfluoride in tetrahydrofuran (1.1 mL). The mixture was stirred for 2hours. After diluting the reaction with water (20 mL) and acidifyingwith 1N hydrochloric acid, the resulting precipitate was filtered,washed with water and hexane/ether, and air dried to give 0.28 g of thetitle compound as a white solid, m.p. 134-142° C.

200 MHz NMR (CDCl₃): δ 6 1.38 (t, 3H, CH₃); 2.89 (s, 3H, CH₃); 3.24 (s,6H, NCH₃); 4.36 (q, 2H, OCH₂); 4.74 (q, 2H, CH₂); 7.4 (m, 4H, arom. andNH); and 12.38 (s, 1H, NH).

IR (nujol) 1710, 1695 cm⁻¹

EXAMPLE 6 Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate

A solution of methyl2-(dimethyl-(1,1-dimethylethyl)silylamino)-3-methylbenzoate (0.68 g) and-phenyl-N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamate(0.79 g) in tetrahydrofuran (10 mL) was treated with 1Mtetrabutylammonium fluoride in tetrahydrofuran (2.2 mL). The mixture wasstirred for 1 hour. After diluting the reaction with water (30 mL) andacidifying with 1N hydrochloric acid, the resulting precipitate wasfiltered, washed with water and chlorobutane/hexane, and air dried togive 0.58 g of the title compound as a white solid, m.p. 151-159° C.with decomposition. Another sample previously prepared by this methodmelted at 150-160° C. with decomposition.

300 MHz NMR (DMSO): δ6 3.04 (s, 3H, CH₃); 3.46 (s, 6H, NCH₃); 4.10 (s,3H, OCH₃); 5.32 (m, 2H, CH₂); 7.78 (d, 1H, arom.); 7.84 (d, 1H, arom.);7.98 (m, 1H, arom.); 11.1 (s, 1H, NH); and 13.1 (s, 1H, NH).

IR (nujol) 1730 cm⁻¹.

The following compounds may be prepared by one skilled in the art usingthe general methods described earlier and exemplified in Examples 1 to6.

                  TABLE 1                                                         ______________________________________                                         ##STR14##                     I                                              R.sub.1       R               X                                               ______________________________________                                        CH.sub.3      CH.sub.3        NHCH.sub.3                                      CH.sub.3      CH.sub.3        N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.3                                                                    NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.3                                                                    N(CH.sub.3).sub.2                               CH.sub.3      CH(CH.sub.3).sub.2                                                                            NHCH.sub.3                                      CH.sub.3      CH(CH.sub.3).sub.2                                                                            NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH(CH.sub.3).sub.2                                                                   NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH(CH.sub.3).sub.2                                                                   N(CH.sub.3).sub.2                               CH.sub.3      CH(CH.sub.3)CH.sub.2 CH.sub.3                                                                 NHCH.sub.3                                      CH.sub.3      CH(CH.sub.3)CH.sub.2 CH.sub.3                                                                 N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CHCH.sub.2                                                                           NHCH.sub.3                                      CH.sub.3      CH.sub.2 CHCH.sub.2                                                                           N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CCH    NHCH.sub.3                                      CH.sub.3      CH.sub.2 CCH    N(CH.sub.3).sub.2                               CH.sub.3                                                                                     ##STR15##      NHCH.sub.3                                      CH.sub.3                                                                                     ##STR16##      N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.2 OCH.sub.3                                                                   NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.2 OCH.sub.3                                                                   N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                          N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.2 SCH.sub.3                                                                   NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.2 SCH.sub.3                                                                   N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                                          NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.2 CN                                                                          NHCH.sub.3                                      CH.sub.3      CH.sub.2 CH.sub.2 CN                                                                          N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub. 2 Cl                                                                         N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.2 F                                                                           N(CH.sub.3).sub.2                               CH.sub.3      CH.sub.2 CH.sub.2 Br                                                                          N(CH.sub.3).sub.2                               CH.sub.2 CH.sub.3                                                                           CH.sub.3        N(CH.sub.3).sub.2                               CH.sub.2 CH.sub.3                                                                           CH.sub.3        NHCH.sub.3                                      CH.sub.2 CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      CH.sub.2 CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               CH.sub.2 CH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                            N(CH.sub.3).sub.2                               CH.sub.2 CH.sub.3                                                                           CH.sub.2 CHCH.sub.2                                                                           N(CH.sub.3).sub.2                               CH.sub.2 CH.sub.3                                                                           CH.sub.2 CH.sub.2 Cl                                                                          N(CH.sub.3).sub.2                               CF.sub.3      CH.sub.3        N(CH.sub.3).sub.2                               CF.sub.3      CH.sub.3        NHCH.sub.3                                      CF.sub.3      CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      CF.sub.3      CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               CF.sub.3                                                                                     ##STR17##      N(CH.sub.3).sub.2                               CF.sub.3                                                                                     ##STR18##      NHCH.sub.3                                      CF.sub.3      CH.sub.2 CN     NHCH.sub.3                                      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.3        NHCH.sub.3                                      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      CH.sub.2 CH.sub.2 Cl                                                                        CH.sub.2 CH.sub. 2 CH.sub.2 CH.sub.3                                                          NHCH.sub.3                                      CH.sub.2 CN   CH.sub.3        NHCH.sub.3                                      CH.sub.2 CN   CH.sub.3        N(CH.sub.3).sub.2                               CH.sub.2 CN   CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               CH.sub.2 CN   CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      CH.sub.2 CN   CH.sub.2 CH.sub.2 CH.sub.3                                                                    NHCH.sub.3                                      CH.sub.2 CN   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           NHCH.sub.3                                      CH.sub.2 CN   CH.sub.2 CHCH.sub.2                                                                           NHCH.sub.3                                      CH.sub.2 CN   CH.sub.2 CHCH.sub.2                                                                           N(CH.sub.3).sub.2                               CH.sub.2 CN   CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                          N(CH.sub.3).sub.2                               CH.sub.2 CN   CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                          NHCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                          CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                          CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               CH.sub.2 OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                            N(CH.sub.3).sub.2                               CH.sub.2 OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                            NHCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                           ##STR19##      NHCH.sub.3                                      CH.sub.2 OCH.sub.3                                                                           ##STR20##      N(CH.sub.3).sub.2                               OCH.sub.3     CH.sub.3        N(CH.sub.3).sub.2                               OCH.sub.3     CH.sub.3        NHCH.sub.3                                      OCH.sub.3     CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      OCH.sub.3     CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               OCH.sub.3     CH(CH.sub.3).sub.2                                                                            N(CH.sub.3).sub.2                               OCH.sub.3     CH(CH.sub.3).sub.2                                                                            NHCH.sub.3                                      OCH.sub.3     CH.sub.2 CHCH.sub.2                                                                           NHCH.sub.3                                      OCH.sub.3     CH.sub.2 CHCH.sub.2                                                                           N(CH.sub.3).sub.2                               OCH.sub.3                                                                                    ##STR21##      N(CH.sub.3).sub.2                               OCH.sub.3     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                          N(CH.sub.3).sub.2                               OCH.sub.3     CH.sub.2 CH.sub.2 SCH.sub.3                                                                   N(CH.sub.3).sub.2                               OCH.sub.3     CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                                          N(CH.sub.3).sub.2                               OCH.sub.3     CH.sub.2 CH.sub.2 CN                                                                          N(CH.sub.3).sub.2                               OCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      OCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               OCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.2 OCH.sub.3                                                                   NHCH.sub.3                                      OCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.2 Br                                                                          NHCH.sub.3                                      OCH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3        N(CH.sub.3).sub.2                               OCH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               OCH(CH.sub. 3).sub.2                                                                        CH.sub.3        N(CH.sub.3).sub.2                               OCH(CH.sub.3).sub.2                                                                         CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               OCH(CH.sub.3).sub.2                                                                         CH.sub.2 CH.sub.2 OCH.sub.3                                                                   N(CH.sub.3).sub.2                               SCH.sub.3     CH.sub.3        NHCH.sub.3                                      SCH.sub.3     CH.sub.3        N(CH.sub.3).sub.2                               SCH.sub.3     CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               SCH.sub.3     CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      SCH.sub.3     CH.sub.2 CH.sub.2 CH.sub.3                                                                    NHCH.sub.3                                      SCH.sub.3     CH.sub.2 CCH    NHCH.sub.3                                      SCH.sub.3     CH.sub.2 CH.sub.2 OCH.sub.3                                                                   NHCH.sub.3                                      SCH.sub.2 CH.sub.3                                                                          CH.sub.3        NHCH.sub.3                                      SCH.sub.2 CH.sub.3                                                                          CH.sub.3        N(CH.sub.3).sub.2                               SCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               SCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      SCH.sub.2 CH.sub.3                                                                           ##STR22##      NHCH.sub.3                                      SCH.sub.2 CH.sub.3                                                                           ##STR23##      NH(CH.sub.3).sub.2                              SCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.2 SCH.sub.3                                                                   N(CH.sub.3).sub.2                               SCH.sub.2 CH.sub.3                                                                          CH.sub.2 CH.sub.2 OCH.sub.3                                                                   N(CH.sub. 3).sub.2                              SCH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3        N(CH.sub.3).sub.2                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.2 CH.sub.2 Br                                                                          N(CH.sub.3).sub.2                               SCH(CH.sub.3).sub.2                                                                         CH.sub.3        N(CH.sub.3).sub.2                               SCH(CH.sub.3).sub.2                                                                         CH.sub.2 CH.sub.2 OCH.sub.3                                                                   N(CH.sub.3).sub.2                               SCH(CH.sub.3).sub.2                                                                          ##STR24##      N(CH.sub.3).sub.2                               SC.sub.6 H.sub.5                                                                            CH.sub.3        NHCH.sub.3                                      SC.sub.6 H.sub.5                                                                            CH.sub.3        N(CH.sub.3).sub.2                               SC.sub.6 H.sub.5                                                                            CH.sub.2 CH.sub.3                                                                             NHCH.sub.3                                      SC.sub.6 H.sub.5                                                                            CH.sub.2 CH.sub.3                                                                             N(CH.sub.3).sub.2                               ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

    ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers" , 2nd Ed., Dorland Books,Caldwell, New Jersey, but other solids, either mined or manufactured,may be used. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide," 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well asSisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc., New York, 1964, list surfactants and recommendeduses. All formulations can contain minor amounts of additives to reducefoaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following Examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 7 Wettable Powder

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       80%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    sodium alkylnaphthalenesulfonate                                                                          2%                                                sodium ligninsulfonate      2%                                                synthetic amorphous silica  3%                                                kaolinite                   13%                                               ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 8

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                        50%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    sodium alkylnaphthalenesulfonate                                                                          2%                                                low viscosity methyl cellulose                                                                            2%                                                diatomaceous earth          46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 9

    ______________________________________                                        Granule                                                                       ______________________________________                                        Wettable Powder of Example 8                                                                             5%                                                 attapulgite granules       95%                                                (U.S.S. 20 to 40 mesh; 0.84-0.42 mm)                                          ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 10

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       25%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                             5%                                                sodium alkylnaphthalenesulfonate                                                                          1%                                                calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 11

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       0.1%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    attapulgite granules       99.9%                                              (U.S.S. 20 to 40 mesh, 0.42 to 0.84 mm)                                       ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 12

    ______________________________________                                        Granule                                                                       ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       80%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    wetting agent               1%                                                crude ligninsulfonate salt (containing                                                                    10%                                               5 to 20% of the natural sugars)                                               attapulgite clay            9%                                                ______________________________________                                    

The ingredients are blended and milled to Pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14 to 100 mesh (1410 to 149 microns), andpackaged for use.

EXAMPLE 13

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                        1%                                                ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    N,N-dimethylformamide       9%                                                attapulgite granules        90%                                               (U.S.S. 20 to 40 sieve, 0.42 to 0.84 mm)                                      ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 14

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       40%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    polyacrylic acid thickener  0.3%                                              dodecylphenol polyethylene glycol ether                                                                   0.5%                                              disodium phosphate          1%                                                monosodium phosphate        0.5%                                              polyvinyl alcohol           1.0%                                              water                       56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 15

    ______________________________________                                        Solution                                                                      ______________________________________                                        Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                        5%                                                ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate, sodium salt                                       water                       95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 16

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       99%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    silica aerogel              0.5%                                              synthetic amorphous silica  0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 17

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                        90%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    dioctyl sodium sulfosuccinate                                                                             0.1%                                              synthetic fine silica       9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 18

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       40%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    sodium ligninsulfonate      20%                                               montmorillonite clay        40%                                               ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 19

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                        35%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    blend of polyalcohol carboxylic                                                                           6%                                                esters and oil soluble petroleum sulfonates                                   xylene                      59%                                               ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 20

    ______________________________________                                        Dust                                                                          ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       10%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    attapulgite                 10%                                               Pyrophyllite                80%                                               ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

EXAMPLE 21

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        Ethyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                        25%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    Polyoxyethylene sorbitol hexaoleate                                                                       5%                                                highly aliphatic hydrocarbon oil                                                                          70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 22

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoro-                                                       20%                                               ethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]                              sulfonyl]-3-methylbenzoate                                                    sodium alkylnaphthalenesulfonate                                                                          4%                                                sodium ligninsulfonate      4%                                                low viscosity methyl cellulose                                                                            3%                                                attapulgite                 69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

Utility

The compounds of this invention are particularly useful for the controlof undesired vegetation in sugar beets, fodder beets, and red beets.These are crops that take long time periods to become established. Inthis interval, the crop seedlings must be nurtured carefully, withparticular attention to weed control to prevent damage and yield lossdue to competition. The subject compounds can be used either pre- orpost-emergence and will control numerous problem weeds includingcatchweed bedstraw (Galium aparine) wild buckwheat (Polygonumconvolvulus), wild mustard (Sinapsis arvensis) and bIackgrass(Alopercurus mysoroides).

The rate of application for these compounds is determined by a number offactors including the weeds to be controlled, weather and climate, soiltype, time of application, age and size of crop and weeds, method ofapplication, etc. In general terms, the rate will vary between about 0.5and 1000 g/ha, with preferred rates of about 10 to 125 g/ha. The rate tobe used in any given situation can be selected by one with ordinaryskill in the art.

These compounds can and will often be used in mixtures with one or moreother herbicides. They may be mixed with other herbicides selective onbeet crops, including metamitron, phenmedipham, desmedipham,chloridazon, lenacil, ethofumesate, cycloate, clopyralid, diallate,triallate, diclofop-methyl, quizalofop-ethyl, fuzalifop-butyl,haloxafop, sethoxidym and alloxidym.

The selective properties of these compounds were discovered ingreenhouse tests. The results of these tests clearly show the activityand selectivity of these compounds and are shown in the tables below.

    ______________________________________                                        COMPOUNDS                                                                      ##STR25##                                                                    CMPD   R.sub.1 R             X       m.p. (°C.)                        ______________________________________                                        1      CH.sub.3                                                                              CH.sub.2 CH.sub.3                                                                           N(CH.sub.3).sub.2                                                                     134-142                                  2      CH.sub.3                                                                              CH.sub.3      NHCH.sub.3                                                                            123-129(d)                               3      CH.sub.3                                                                              CH.sub.3      N(CH.sub.3).sub.2                                                                     150-160(d)                               4      CH.sub.3                                                                              (CH.sub.2).sub.2 CH.sub.3                                                                   N(CH.sub.3).sub.2                                                                     143-150(d)                               5      CH.sub.3                                                                              (CH.sub.2).sub.2 CH.sub.3                                                                   NHCH.sub.3                                                                            159-163                                  6      CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                          NHCH.sub.3                                                                            185-186                                  7      CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                          N(CH.sub.3).sub.2                                                                     155-156                                  8      CH.sub.3                                                                              CH.sub.2 -cyclo-C.sub.3 H.sub.5                                                             N(CH.sub.3).sub.2                                                                     105-115(d)                               9      CH.sub.3                                                                              CH.sub.2 CH.sub.3                                                                           NHCH.sub.3                                                                            149- 152                                 10     CH.sub.3                                                                              C(CH.sub.3).sub.3                                                                           NHCH.sub.3                                                                            181-183                                  11     CH.sub.3                                                                              C(CH.sub.3).sub.3                                                                           N(CH.sub.3).sub.2                                                                      82-89                                   ______________________________________                                    

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), cheatgrass (Bromus secalinus) or downy brome (Bromustectorum), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton(Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setariafaberi), morningglory (Ipomoea spp.), rice (Oryz sativa), sorghum(Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris),velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and wildoat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers wereplanted and treated preemergence with test chemicals dissolved in anon-phytotoxic solvent. At the same time, these crop and weed specieswere also treated with postemergence applications of test chemicals.Plants ranged in height from two to eighteen cm (two to three leafstage) for postemergence treatments. Treated Plants and controls weremaintained in a greenhouse for sixteen days, after which all specieswere compared to controls and visually evaluated. The ratings,summarized in Table A, are based on a scale of 0 to 10 where 0 is noeffect and 10 is complete control. A dash (--) response means no test.The accompanying descriptive symbols have the following meanings:

C=chlorosis/necrosis;

G=growth retardation; and

H=formative effect.

                                      TABLE A                                     __________________________________________________________________________    POSTEMERGENCE                                                                         Cmpd 1   2        3        4       5                                  RATE (g/ha)                                                                           50   10  50   10  50   10  50  10  50  10                             __________________________________________________________________________    Barley   3C, 9G                                                                            8G   3C, 9G                                                                            3C, 9G                                                                             2C, 9G                                                                            3C, 9G                                                                            8G  4G  9G  7G                             Barnyardgrass                                                                          9C  3C, 9H                                                                             9C  3C, 9G                                                                             9C  4C, 9H                                                                            3C, 7H                                                                            3C, 6G                                                                            3C, 7G                                                                            3C, 5G                         Cheatgrass                                                                            --   --   2C, 9G                                                                            3C, 8G                                                                             5C, 9G                                                                            4C, 9G                                                                            4G  0   3C, 9G                                                                            0                              Cocklebur                                                                             10C  3C, 9H                                                                             9C  3C, 7H                                                                            10C  4C, 9G                                                                            4C, 9G                                                                            2C, 7G                                                                            3C, 8G                                                                            2C, 7G                         Corn     3C, 9G                                                                            3C, 9G                                                                             3C, 9G                                                                            3C, 9H                                                                             9G  3C, 9H                                                                            3C, 7H                                                                            3G  3C, 5G                                                                            4G                             Cotton   9G  3C, 6G                                                                             5C, 9G                                                                            4C, 9H                                                                             4C, 9G                                                                            4C, 9H                                                                            3C, 8H                                                                            8H  4C, 9H                                                                            3C, 8H                         Crabgrass                                                                              0   0    3C, 7G                                                                            3G   3C, 8G                                                                            2C, 4G                                                                            0   0   2G  0                              Downy brome                                                                            5C, 9G                                                                            3C, 9G                                                                            --   --  --   --  --  --  --  --                             Giant foxtail                                                                          3C, 7G                                                                            2G   3C, 9G                                                                            3C, 7G                                                                             3C, 9G                                                                            3C, 6G                                                                            2G  0   5G  2G                             Morningglory                                                                          10C  4C, 9H                                                                             9C  5C, 9G                                                                             9C  4C, 8H                                                                            5C, 9G                                                                            4C, 8H                                                                            5C, 9G                                                                            3C, 8H                         Nutsedge                                                                               5G  --   2C, 9G                                                                            --   9C  9C  0   0   --  0                              Rice     9C  5C, 9G                                                                             9C  9C   5C, 9G                                                                            5C, 9G                                                                            3C, 7G                                                                            2G  3C, 7G                                                                            5G                             Sorghum  4C, 9G                                                                            9H   5C, 9G                                                                            5C, 9G                                                                             5C, 9G                                                                            4C, 9G                                                                            2C, 3G                                                                            2G  2C, 5G                                                                            2G                             Soybean  4C, 9G                                                                            4C, 9G                                                                             9C  4C, 9G                                                                             4C, 9G                                                                            4C, 9G                                                                            3C, 8H                                                                            3C, 4G                                                                            4C, 9G                                                                            4C, 8H                         Sugar beet                                                                             0   0    2G  0    4G  0   0   0   3G  0                              Velvetleaf                                                                             9C  4C, 8H                                                                            10C  3C, 8G                                                                            10C  4C, 9G                                                                            2C, 8H                                                                            2G  8G  2C, 6G                         Wheat    4C, 9G                                                                            7G   9G  9G   3C, 9G                                                                            9G  3G  0   4G  2G                             Wild oat                                                                               4C, 9G                                                                            3C, 6G                                                                             3C, 8G                                                                            3C, 5G                                                                             3C, 8G                                                                            3C, 5G                                                                            3G  0   3C, 4G                                                                            1C                             __________________________________________________________________________    POSTEMERGENCE                                                                                    6       7       8       9                                             RATE (g/ha)                                                                           50  10  50  10  50  10  50  10                             __________________________________________________________________________               Barley  4C, 9G                                                                            3C, 8H                                                                            9G  7G  4G  0   9G  8G                                        Barnyardgrass                                                                         3C, 9H                                                                            3C, 7H                                                                            3C, 8H                                                                            2C, 6H                                                                            2C, 4G                                                                            0   9G  3C, 7H                                    Cheatgrass                                                                            7G  6G  7G  4G  0   0   9G  3G                                        Cocklebur                                                                             3C, 8H                                                                            3C, 8H                                                                            5C, 9G                                                                            3C, 8G                                                                            3C, 4G                                                                            1C, 2G                                                                            4C, 9G                                                                            4C, 7G                                    Corn    3C, 8H                                                                            3C, 8G                                                                            3C, 9G                                                                            2C, 7G                                                                            2C, 4G                                                                            0   3C, 9H                                                                            3C, 6G                                    Cotton  4C, 9G                                                                            9H  3C, 9G                                                                            3G  1C, 3G                                                                            0   4C, 8G                                                                            3C, 7G                                    Crabgrass                                                                             3G  0   0   0   0   0   6G  3G                                        Downy brome                                                                           --  --  --  --  --  --  --  --                                        Giant foxtail                                                                         3G  0   2G  0   0   0   7G  3G                                        Morningglory                                                                          4C, 9G                                                                            3C, 8H                                                                            3C, 9G                                                                            3C, 8G                                                                            3C, 6G                                                                            2C  9C  4C, 8G                                    Nutsedge                                                                              --  --  --  --  0   0   9G  4G                                        Rice    4C, 8G                                                                            3C, 7G                                                                            3C, 8G                                                                            2C, 3G                                                                            2C, 2G                                                                            0   5C, 9G                                                                            5C, 9G                                    Sorghum 4C, 9G                                                                            4C, 9G                                                                            3C, 8H                                                                            3C, 8G                                                                            6G  0   9G  9G                                        Soybean 5C, 9H                                                                            4C, 8G                                                                            4C, 9G                                                                            4C, 8G                                                                            3C, 4G                                                                            0   5C, 9G                                                                            5C, 9G                                    Sugar beet                                                                            1H  0   0   0   0   0   0   0                                         velvetleaf                                                                            2C, 8H                                                                            2C, 5G                                                                            3C, 8H                                                                            0   0   0   9C  4C, 9G                                    Wheat   8G  6G  8G  7G  3G  0   9G  9G                                        Wild oat                                                                              9G  3C, 7G                                                                            2C, 6G                                                                            2C, 5G                                                                            0   0   3C, 9G                                                                            7G                             __________________________________________________________________________    PREEMERGENCE                                                                          Cmpd 1 2       3       4    5      6                                  RATE (g/ha)                                                                           50  10 50  10  50  10  50 10                                                                              50  10 50  10                             __________________________________________________________________________    Barley  9G  0  3C, 8G                                                                            3C, 8G                                                                            9G  4G  2G 0 8G  3G 8G  2G                             Barnyardgrass                                                                         2G  0  3C, 8H                                                                            7H  3C, 8H                                                                            1H  3G 0 6G  0  3C, 7H                                                                            3G                             Cheatgrass                                                                            --  -- 8G  4G  3C, 8H                                                                            0   0  0 6G  0  3C, 7G                                                                            5G                             Cocklebur                                                                             3C, 4H                                                                            0  4G  0   2C, 2H                                                                            0   3G 0 8G  2H 3C, 5H                                                                            3G                             Corn    3C, 7G                                                                            2G 4C, 9H                                                                            3C, 3G                                                                            4C, 9H                                                                            4G  3G 0 3C, 7G                                                                            3G 3C, 8G                                                                            3C, 7G                         Cotton  0   0  0   2G  2G  0   5G 0 2G  0  3G  0                              Crabgrass                                                                             0   0  3C, 5G                                                                            2G  3C, 6G                                                                            4G  0  0 2G  0  3C, 7G                                                                            2G                             Downy brome                                                                           5G  0  --  --  --  --  -- --                                                                              --  -- --  --                             Giant foxtail                                                                         2G  0  3C, 7H                                                                            5G  2C, 3G                                                                            0   0  0 2G  0  2C, 7G                                                                            2G                             Morningglory                                                                          3C, 3H                                                                            0  4C, 9G                                                                            5G  3C, 4H                                                                            0   2G 0 7G  3G 9H  3G                             Nutsedge                                                                              0   0  3C, 3G                                                                            0   4G  0   7G 0 0   0  9G  0                              Rice    3C, 5G                                                                            0  5C, 9H                                                                            4G  7G  4G  2G 0 7G  2G 4G  0                              Sorghum 3C, 7G                                                                            0  4C, 9H                                                                            3C, 7G                                                                            4C, 9H                                                                            2C, 5G                                                                            3G 0 3C, 7G                                                                            2G 3C, 8H                                                                            3C, 5G                         Soybean 2C, 2H                                                                            1C 4C, 6H                                                                            3C, 3G                                                                            3H  2G  3G 0 3C, 5G                                                                            3G 3C, 6H                                                                            2H                             Sugar beet                                                                            0   0  4G  0   0   0   2G 0 0   0  0   0                              Velvetleaf                                                                            2H  0  4H  0   5H  0   3G 0 6G  0  6H  2G                             Wheat   4G  0  2C, 8G                                                                            3G  8G  0   0  0 4G  0  2C, 3G                                                                            0                              Wild oat                                                                              2C, 5G                                                                            0  2G  0   2G  0   0  0 5G  0  6G  3G                             __________________________________________________________________________    PREEMERGENCE                                                                                               7       8     9                                                       RATE (g/ha)                                                                           50  10  50 10 50  10                             __________________________________________________________________________                         Barley  2C, 5G                                                                            0   0  0  8G  8G                                                  Barnyardgrass                                                                         3C, 7G                                                                            0   0  0  3C, 7H                                                                            2G                                                  Cheatgrass                                                                            6G  0   0  0  6G  0                                                   Cocklebur                                                                             7H  0   0  0  3C, 7H                                                                            0                                                   Corn    3C, 8G                                                                            2C, 4G                                                                            0  0  3C, 9G                                                                            3C, 4G                                              Cotton  2G  0   0  0  0   0                                                   Crabgrass                                                                             5G  0   0  0  0   0                                                   Downy brome                                                                           --  --  -- -- --  --                                                  Giant foxtail                                                                         4G  0   2G 0  5G  2G                                                  Morningglory                                                                          8H  0   0  0  9G  3C, 4G                                              Nutsedge                                                                              0   0   0  0  0   0                                                   Rice    4G  0   0  0  2C, 5G                                                                            2G                                                  Sorghum 3C, 8G                                                                            2C, 2G                                                                            0  0  4C, 9G                                                                            2C, 4H                                              Soybean 2C, 4H                                                                            2C, 2G                                                                            0  0  4C, 8H                                                                            2G                                                  Sugar beet                                                                            0   0   0  0  0   0                                                   Velvetleaf                                                                            7H  0   2H 0  6H  3H                                                  Wheat   2G  0   0  0  8G  2G                                                  Wild oat                                                                              6G  0   0  0  7G  2G                             __________________________________________________________________________

TEST B

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), blackgrass (Alopecurus myosuroides), chickweed (Stellariamedia), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton(Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromustectorum), giant foxtail (Setaria faberi), green foxtail (Setariaviridis), jimsonweed (Datura stramonium), johnsongrass (Sorghumhalepense), lambsquarters (Chenopodium album), morningglory (Ipomoeaspp.), rape (Brassica napus), rice (Oryza sativa), sicklepod (Cassiaobtusifolia), soybean (Glycine max), sugar beet (Beta vulgaris), teaweed(Sida spinosa), velvetleaf (Abutilon theophrasti), wheat (Titicumaestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) tubers were planted andtreated preemergence with test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were also treatedwith postemergence applications of test chemicals. Plants ranged inheight from two to eighteen cm (two to three leaf stage) forpostemergence treatments. Treated plants and controls were maintained ina greenhouse for approximately 24 days, after which all species werecompared to controls and visually evaluated. The ratings, summarized inTable B, are based on a scale of 0 to 100 where 0 is no effect and 100is complete control. A dash (--) response means no test.

                                      TABLE B                                     __________________________________________________________________________    POSTEMERGENCE                                                                          Cmpd 1     2          3           4       5                          RATE (g/ha)                                                                            250                                                                              62 16 4 250                                                                              62 16 4 250                                                                              62 16 4  62                                                                              16                                                                              4 1 250                                                                              62 16 4                 __________________________________________________________________________    Barley   100                                                                              80 60 30                                                                              90 90 80 30                                                                              90 90 60 40 60                                                                              30                                                                              0 0 70 60     50                                                                     30                      Barnyardgrass                                                                          100                                                                              90 80 30                                                                              100                                                                              90 60 40                                                                              100                                                                              100                                                                              70 30 50                                                                              30                                                                              0 0 80 50     30                                                                     0                       Blackgrass                                                                             100                                                                              100                                                                              30 0 95 95 60 50                                                                              100                                                                              90 90 60 60                                                                              30                                                                              0 0 90 80     70                                                                     30                      Chickweed                                                                              100                                                                              90 70 40                                                                              80 30 0  0 80 70 20 0  30                                                                              0 0 0 50 30     0                                                                      0                       Cocklebur                                                                              100                                                                              90 70 0 80 30 0  0 70 40 20 0  60                                                                              30                                                                              0 0 50 40     30                                                                     0                       Corn     100                                                                              100                                                                              90 70                                                                              100                                                                              100                                                                              80 60                                                                              100                                                                              100                                                                              60 50 30                                                                              0 0 0 0  0      0                                                                      0                       Cotton   80 70 20 10                                                                              90 90 80 50                                                                              90 90 80 70 30                                                                              0 0 0 50 30     0                                                                      0                       Crabgrass                                                                              90 20 0  0 70 30 20 0 60 40 20 0  0 0 0 0 40 30     20                                                                     0                       Downy brome                                                                            100                                                                              100                                                                              100                                                                              60                                                                              95 95 90 40                                                                              95 95 70 50 60                                                                              30                                                                              0 0 70 50     30                                                                     0                       Giant foxtail                                                                          70 40 0  0 100                                                                              40 20 0 90 70 0  0  0 0 0 0 50 30     0                                                                      0                       Green foxtail                                                                          40 10 0  0 90 60 40 20                                                                              50 40 0  0  0 0 0 0 40 20     0                                                                      0                       Jimsonweed                                                                             100                                                                              100                                                                              90 70                                                                              100                                                                              90 70 50                                                                              100                                                                              90 90 80 70                                                                              50                                                                              30                                                                              0 50 40     30                                                                     20                      Johnsongrass                                                                           -- 100                                                                              80 40                                                                              100                                                                              90 60 40                                                                              100                                                                              90 40 30 60                                                                              30                                                                              0 0 70 50     40                                                                     30                      Lambsquarters                                                                          100                                                                              80 30 --                                                                              50 30 0  0 90 0  0  0  70                                                                              60                                                                              50                                                                              40                                                                              90 70     50                                                                     0                       Morningglory                                                                           100                                                                              90 80 50                                                                              100                                                                              100                                                                              100                                                                              0 100                                                                              100                                                                              90 80 90                                                                              50                                                                              30                                                                              0 80 50     30                                                                     0                       Nutsedge 100                                                                              100                                                                              90 40                                                                              100                                                                              100                                                                              100                                                                              0 100                                                                              100                                                                              100                                                                              100                                                                              50                                                                              30                                                                              0 0 90 30     0                                                                      0                       Rape     100                                                                              100                                                                              100                                                                              80                                                                              90 90 30 0 100                                                                              100                                                                              80 50 90                                                                              70                                                                              50                                                                              30                                                                              100                                                                              100    100                                                                    100                     Rice     100                                                                              100                                                                              80 50                                                                              100                                                                              100                                                                              100                                                                              90                                                                              100                                                                              100                                                                              100                                                                              70 30                                                                              0 0 0 60 40     30                                                                     0                       Sicklepod                                                                              100                                                                              100                                                                              90 80                                                                              100                                                                              90 90 0 100                                                                              100                                                                              90 70 0 0 0 0 30 0      0                                                                      0                       Soybean  90 90 80 80                                                                              90 90 90 70                                                                              90 90 80 50 90                                                                              60                                                                              30                                                                              0 90 70     60                                                                     50                      Sugar beet                                                                             20 0  0  0 70 0  0  0 40 0  0  0  0 0 0 0 30 0      0                                                                      0                       Teaweed  90 80 70 50                                                                              80 30 0  0 70 50 20 0  40                                                                              30                                                                              20                                                                              0 50 30     0                                                                      0                       Velvetleaf                                                                             100                                                                              100                                                                              80 80                                                                              90 90 70 50                                                                              100                                                                              100                                                                              100                                                                              90 60                                                                              30                                                                              0 0 90 70     50                                                                     40                      Wheat    90 70 70 40                                                                              90 90 80 40                                                                              90 90 60 30 40                                                                              0 0 0 40 30     0                                                                      0                       Wild buckwheat                                                                         100                                                                              80 70 20                                                                              80 80 20 0 100                                                                              50 0  0  0 0 0 0 60 0      0                                                                      0                       Wild oat 100                                                                              60 60 30                                                                              95 60 40 0 95 80 40 20 30                                                                              0 0 0 70 60     30                                                                     0                       __________________________________________________________________________                                  6          7          9                                              RATE (g/ha)                                                                            250                                                                              62 16 4 250                                                                              62 16 4 250                                                                              62 16 4                __________________________________________________________________________                         Barley   70 60 50 40                                                                              90 70 60 50                                                                              80 60 60 60                                    Barnyardgrass                                                                          50 40 30 20                                                                              80 70 60 30                                                                              80 75 70 50                                    Blackgrass                                                                             100                                                                              100                                                                              90 70                                                                              90 80 70 30                                                                              90 80 70 40                                    Chickweed                                                                              70 60 50 30                                                                              90 80 50 30                                                                              80 70 50 30                                    Cocklebur                                                                              75 70 60 50                                                                              100                                                                              90 80 70                                                                              90 80 60 30                                    Corn     70 60 50 40                                                                              75 70 60 50                                                                              90 80 70 50                                    Cotton   70 60 40 30                                                                              80 70 60 50                                                                              70 60 50 40                                    Crabgrass                                                                              60 50 40 30                                                                              50 30 0  0 40 30 0  0                                     Downy brome                                                                            80 70 60 40                                                                              90 70 60 50                                                                              90 80 70 60                                    Giant foxtail                                                                          30 30 20 20                                                                              60 30 0  0 60 50 30 0                                     Green foxtail                                                                          50 40 30 20                                                                              60 30 0  0 80 70 50 40                                    Jimsonweed                                                                             90 85 80 70                                                                              100                                                                              100                                                                              90 80                                                                              100                                                                              100                                                                              90 70                                    Johnsongrass                                                                           90 80 70 60                                                                              90 80 70 50                                                                              90 80 70 60                                    Lambsquarters                                                                          90 80 70 60                                                                              90 80 70 60                                                                              40 30 0  0                                     Morningglory                                                                           85 80 75 70                                                                              100                                                                              100                                                                              100                                                                              90                                                                              100                                                                              100                                                                              90 80                                    Nutsedge 70 60 50 30                                                                              90 80 70 60                                                                              100                                                                              90 60 30                                    Rape     100                                                                              100                                                                              100                                                                              70                                                                              100                                                                              100                                                                              90 70                                                                              100                                                                              100                                                                              100                                                                              90                                    Rice     80 70 60 50                                                                              80 70 60 50                                                                              70 70 70 70                                    Sicklepod                                                                              80 70 60 50                                                                              95 90 80 70                                                                              100                                                                              80 70 60                                    Soybean  90 85 80 70                                                                              100                                                                              90 80 70                                                                              100                                                                              100                                                                              90 60                                    Sugar beet                                                                             20 0  0  0 20 0  0  0 0  0  0  0                                     Teaweed  70 60 50 30                                                                              70 60 50 40                                                                              80 70 60 50                                    Velvetleaf                                                                             95 90 80 70                                                                              95 90 80 70                                                                              100                                                                              100                                                                              90 70                                    Wheat    60 50 30 0 100                                                                              70 50 30                                                                              60 50 50 50                                    Wild buckwheat                                                                         100                                                                              100                                                                              90 70                                                                              90 80 70 60                                                                              -- -- -- --                                    Wild oat 80 75 70 60                                                                              90 70 50 0 70 60 50 40               __________________________________________________________________________    PREEMERGENCE                                                                           Cmpd 1   2           3           4        5                          RATE (g/ha)                                                                            250                                                                              62 16 250                                                                              62 16 4  250                                                                              62 16 4  250                                                                              62 16 250                                                                              62 16 4                 __________________________________________________________________________    Barley   90 80 40 70 60 20 0  80 70 40 0  30 0  0  70 50 0  0                 Barnyardgrass                                                                          100                                                                              100                                                                              60 100                                                                              70 20 0  70 20 0  0  90 60 30 90 70 50 0                 Blackgrass                                                                             80 -- 40 80 50 30 0  70 70 40 30 80 50 0  90 60 30 0                 Chickweed                                                                              90 80 50 30 20 0  0  70 70 30 30 60 30 0  70 50 30 0                 Cocklebur                                                                              90 80 30 90 30 0  0  60 40 30 0  80 30 0  70 50 30 0                 Corn     100                                                                              90 70 100                                                                              70 70 20 100                                                                              100                                                                              30 0  60 20 0  80 60 0  0                 Cotton   30 20 0  80 20 0  0  0  0  0  0  0  0  0  0  0  0  0                 Crabgrass                                                                              50 50 30 50 30 30 0  90 80 70 0  80 50 30 100                                                                              80 30 0                 Downy brome                                                                            90 80 40 100                                                                              70 20 0  100                                                                              40 20 0  70 30 0  70 50 0  0                 Giant foxtail                                                                          90 70 40 90 50 20 0  70 30 0  0  60 30 0  90 80 50 30                Green foxtail                                                                          100                                                                              80 60 90 90 70 20 70 30 0  0  80 30 0  90 70 50 0                 Jimsonweed                                                                             100                                                                              50 30 90 50 20 0  70 40 30 0  70 30 0  70 50 30 0                 Johnsongrass                                                                           100                                                                              100                                                                              90 90 80 20 0  90 80 40 0  60 30 0  80 60 30 0                 Lambsquarters                                                                          100                                                                              60 20 80 70 70 0  80 70 50 0  90 60 30 90 80 70 60                Morningglory                                                                           100                                                                              80 40 100                                                                              60 20 0  70 70 0  0  60 30 0  90 60 50 30                Nutsedge 100                                                                              70 20 30 20 0  0  40 -- 20 0  50 30 0  90 70 0  0                 Rape     100                                                                              90 50 100                                                                              50 0  0  100                                                                              70 20 0  70 50 30 90 70 30 0                 Rice     100                                                                              80 30 70 30 20 0  90 60 20 0  40 0  0  40 20 0  0                 Sicklepod                                                                              100                                                                              60 50 30 20 0  0  40 20 0  0  30 0  0  70 50 30 0                 Soybean  90 50 30 100                                                                              20 0  0  30 0  0  0  20 0  0  60 30 0  0                 Sugar beet                                                                             70 30 0  70 20 0  0  40 20 0  0  30 0  0  30 0  0  0                 Teaweed  80 60 30 50 40 20 0  100                                                                              100                                                                              30 0  70 50 30 70 60 50 30                Velvetleaf                                                                             90 80 70 80 20 -- -- 80 80 0  0  90 50 0  70 30 0  0                 Wheat    90 70 40 80 50 20 0  70 40 20 0  40 0  0  60 30 0  0                 Wild buckwheat                                                                         90 60 20 90 80 80 20 90 80 80 80 0  0  0  0  0  0  0                 Wild oat 60 60 20 60 20 0  0  80 50 30 0  40 0  0  40 30 0  0                 __________________________________________________________________________                                     6         7         9                                                RATE (g/ha)                                                                            250                                                                              62 16                                                                              4 250                                                                              62 16                                                                              4 250                                                                              62 16                                                                              4                __________________________________________________________________________                            Barley   90 80 70                                                                              30                                                                              70 60 30                                                                              0 90 70 50                                                                              30                                       Barnyardgrass                                                                          100                                                                              90 50                                                                              30                                                                              90 80 50                                                                              30                                                                              100                                                                              90 80                                                                              30                                       Blackgrass                                                                             100                                                                              100                                                                              90                                                                              70                                                                              90 80 70                                                                              30                                                                              100                                                                              100                                                                              90                                                                              50                                       Chickweed                                                                              100                                                                              100                                                                              90                                                                              70                                                                              100                                                                              100                                                                              90                                                                              70                                                                              70 50 30                                                                              0                                        Cocklebur                                                                              90 70 50                                                                              30                                                                              70 60 50                                                                              0 90 70 40                                                                              0                                        Corn     100                                                                              80 70                                                                              20                                                                              90 60 30                                                                              0 90 80 70                                                                              30                                       Cotton   60 0  0 0 30 20 0 0 50 40 0 0                                        Crabgrass                                                                              80 50 30                                                                              0 80 50 30                                                                              0 80 30 0 0                                        Downy brome                                                                            100                                                                              100                                                                              80                                                                              50                                                                              100                                                                              80 50                                                                              0 100                                                                              90 70                                                                              60                                       Giant foxtail                                                                          80 50 30                                                                              0 60 30 0 0 90 70 30                                                                              0                                        Green foxtail                                                                          80 50 30                                                                              0 70 30 0 0 90 70 50                                                                              30                                       Jimsonweed                                                                             90 80 70                                                                              60                                                                              90 70 50                                                                              30                                                                              90 70 50                                                                              30                                       Johnsongrass                                                                           90 80 70                                                                              50                                                                              80 70 30                                                                              0 95 90 80                                                                              50                                       Lambsquarters                                                                          100                                                                              100                                                                              90                                                                              80                                                                              100                                                                              100                                                                              50                                                                              30                                                                              90 70 50                                                                              0                                        Morningglory                                                                           90 80 70                                                                              60                                                                              90 70 50                                                                              30                                                                              90 80 70                                                                              50                                       Nutsedge 90 60 30                                                                              0 70 50 30                                                                              0 100                                                                              50 0 0                                        Rape     100                                                                              100                                                                              90                                                                              70                                                                              100                                                                              100                                                                              70                                                                              30                                                                              100                                                                              100                                                                              90                                                                              70                                       Rice     100                                                                              100                                                                              80                                                                              30                                                                              80 60 30                                                                              0 100                                                                              80 50                                                                              30                                       Sicklepod                                                                              90 70 60                                                                              50                                                                              70 60 0 0 80 70 40                                                                              0                                        Soybean  80 40 0 0 70 30 0 0 70 60 40                                                                              0                                        Sugar beet                                                                             90 70 60                                                                              50                                                                              50 40 30                                                                              0 50 30 0 0                                        Teaweed  90 80 --                                                                              50                                                                              90 70 40                                                                              30                                                                              80 70 50                                                                              0                                        Velvetleaf                                                                             90 70 50                                                                              30                                                                              80 70 50                                                                              0 100                                                                              100                                                                              95                                                                              90                                       Wheat    90 60 30                                                                              0 80 30 0 0 100                                                                              70 50                                                                              30                                       Wild buckwheat                                                                         95 90 85                                                                              80                                                                              100                                                                              70 60                                                                              50                                                                              -- -- --                                                                              --                                       Wild oat 80 50 30                                                                              0 70 50 30                                                                              0 70 60 50                                                                              30               __________________________________________________________________________

TEST C

Seeds selected from crop and weed species consisting of annual bluegrass(Poa annua), barley (Hordeum vulgare), black nightshade (Solanumnigrum), blackgrass (Alopecurues myosuroides), catchweed bedstraw(Galium aparine), chickweed (Stellaria media), green foxtail (Setariaviridis), Italian ryegrass (Lolium multiflorum), knotweed (polygonumaviculare), kochia (Kochia scoparia), lambsquarters (Chenopodium album),pigweed (Amaranthus retroflexus), rape (Brassica napus), scentlesschamomile (Matricaria inodora), smartweed (Polygonum persicaria),speedwell (Veronica persica), sugar beet (Beta vulgaris), viola (Violaarvensis), wheat (Triticum aestivum), wild buckwheat (Polygonumconvolvulus), wild mustard (Brassica spp.), wild oat (Avena fatua) andwild radish (Raphanus raphanistrum) were planted and treatedpreemergence with test chemicals dissolved in a non-phytotoxic solvent.Selected species from this list of crops and weeds were also treatedwith postemergence applications of test chemicals. Plants ranged inheight from two to twenty cm (two to three leaf stage) for postemergencetreatments. Treated plants and controls were maintained in a greenhousefor approximately 24 days, after which all species were compared tocontrols and visually evaluated. The ratings, summarized in Table C, arebased on a scale of 0 to 100 where 0 is no effect and 100 is completecontrol. A dash (--) response means no test.

                                      TABLE C                                     __________________________________________________________________________    POSTEMERGENCE                                                                            Cmpd 1      2              3              4                        RATE (g/ha)                                                                              64 32 16 8  250                                                                              125                                                                              64 32 16 250                                                                              125                                                                              64 32 16 64 32 16                                                                              8                __________________________________________________________________________    Annual bluegrass                                                                         70 70 30 0  100                                                                              80 80 40 0  100                                                                              60 60 20 20                          Barley     85 70 75 50 100                                                                              100                                                                              80 80 70 80 80 80 70 50                          Black nightshade                                                                         100                                                                              100                                                                              100                                                                              75                                                        Blackgrass 100                                                                              100                                                                              80 50 100                                                                              100                                                                              100                                                                              100                                                                              0  100                                                                              100                                                                              80 30 20 50 50 30                                                                              0                Catchweed bedstraw                                                                       100                                                                              90 75 0                                20 20 0 0                Chickweed  85 60 40 20 20 20 0  0  0  90 50 20 20 0  30 20 0 0                Green foxtail                                                                            50 0  0  0  80 80 40 40 40 90 80 40 40 20                          Italian ryegrass                                                                         100                                                                              50 50 0                                                         Knotweed                                             -- 20 0 0                Kochia     90 100                                                                              50 20                                                        Lambsquarters                                                                            0  0  0  0  100                                                                              60 60 60 30 100                                                                              30 0  0  0  20 0  --                                                                              --               Pigweed    40 40 30 0  100                                                                              100                                                                              80 60 60 100                                                                              100                                                                              40 20                             Rape       90 90 75 60                                                        Scentless chamomile                                                                      100                                                                              100                                                                              90 30                               70 50 50                                                                              50               Smartweed              100                                                                              100                                                                              90 90 90 100                                                                              100                                                                              100                                                                              90 90                          Speedwell  100                                                                              90 50 30                               80 50 30                                                                              30               Sugar beet 0  0  0  0  50 30 0  0  0  20 0  0  0  0  20 0  0 0                Viola                                                0  0  0 0                Wheat      75 75 50 50                               40 40 30                                                                              30               Wild buckwheat                                                                           100                                                                              80 60 40 100                                                                              100                                                                              100                                                                              100                                                                              80 100                                                                              95 100                                                                              90 90 40 30 20                                                                              0                Wild mustard                                                                             100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                         Wild oat   70 70 50 30 90 80 70 60 50 50 50 0  0  0  50 40 40                                                                              40               Wild radish                                                                              100                                                                              100                                                                              100                                                                              100                                                       __________________________________________________________________________    POSTEMERGENCE                                                                            5           6          7           8 9                             RATE (g/ha)                                                                              125                                                                              64 32 16 125                                                                              64 32                                                                              16 125                                                                              64 32 16                                                                              125                                                                              125                                                                              64 32 16 8                 __________________________________________________________________________    Blackgrass 50 50 50 20 100                                                                              80 80                                                                              50 90 90 50 50                                                                              50 100                                                                              100                                                                              100                                                                              100                                                                              100               Catchweed bedstraw                                                                       70 70 70 30 90 60 60                                                                              30 80 80 80 50                                                                              60 100                                                                              90 90 90 70                Chickweed  0  0  0  0  0  0  0 0  80 50 20 0 30 80 30 30 0  0                 Knotweed   -- 50 50 0  -- 50 --                                                                              50               90 90 90 70 70                Lambsquarters                                                                            -- -- -- 0                        0                                Scentless chamomile                                                                      50 30 20 20 100                                                                              80 80                                                                              80 100                                                                              100                                                                              100                                                                              80                                                                              85 100                                                                              100                                                                              100                                                                              70 50                Speedwell  80 60 50 50 100                                                                              80 80                                                                              30 100                                                                              100                                                                              50 50                                                                              80 100                                                                              100                                                                              100                                                                              80 80                Sugar beet 15 0  0  0  20 0  0 0  0  0  0  0 30 15 0  0  0  0                 Viola      30 30 0  0  70 70 70                                                                              20 100                                                                              100                                                                              50 30                                                                              60 100                                                                              100                                                                              80 50 30                Wheat      50 30 30 30 80 80 70                                                                              50 80 80 70 50                                                                              70 100                                                                              60 50 50 50                Wild buckwheat                                                                           50 50 20 20 100                                                                              100                                                                              80                                                                              70 100                                                                              90 80 80                                                                              70 100                                                                              90 80 70 60                Wild oat   70 50 50 50 100                                                                              70 70                                                                              70 80 80 50 50   100                                                                              90 80 80 80                __________________________________________________________________________    PREEMERGENCE                                                                             Cmpd 1 2    3   4 5    6        7        8 9                       RATE (g/ha)                                                                              64 32 64 32                                                                              64                                                                              32                                                                              64 125                                                                              64                                                                              125                                                                              64 32 125                                                                              64                                                                              32 125                                                                              125                                                                              64 32                __________________________________________________________________________    Annual bluegrass                                                                         75 30 20 0 20                                                                              0                                                     Barley     70 40 70 30                                                                              50                                                                              30                                                    Black nightshade                                                                         30 0                                                               Blackgrass 100                                                                              100                                                                              70 40                                                                              30                                                                              30                                                                              50 90 70                                                                              100                                                                              80 80 80 80                                                                              40 50 100                                                                              100 90               Catchweed bedstraw                                                                       100                                                                              0           90 90 80                                                                              90 90 80 90 90                                                                              90 0  100                                                                              100 90               Chickweed  60 0  0  0 0 0 30 80 50                                                                              80 80 70 80 70                                                                              70 30 100                                                                              100 100              Green foxtail                                                                            0  0  60 20                                                                              20                                                                              0                                                     Italian ryegrass                                                                         60 50                                                              Knotweed                          -- -- 30 0  0 0     100                                                                              100 100              Kochia     0  0                                                               Lambsquarters                                                                            0  0  0  0 50                                                                              0                                                     Pigweed    0  0  40 20                                                                              0 0                                                     Rape       75 20                                                              Scentless chamomile                                                                      90 90          80 90 90                                                                              90 80 80 90 90                                                                              50 0  100                                                                              100 100              Smartweed        90 80                                                                              50                                                                              50                                                    Speedwell  60 --          30 100                                                                              80                                                                              100                                                                              100                                                                              100                                                                              100                                                                              80                                                                              50 50 100                                                                              100 100              Sugar beet 0  0  0  0 30                                                                              0 0  80 30                                                                              90 90 80 30 30                                                                              10 0  100                                                                              80  80               Wheat      40 20          20 70 30                                                                              70 60 40 0  0 0  0  90 90  70               Wild buckwheat                                                                           20 0  20 0 0 0 0  30 30                                                                              90 90 80 85 70                                                                              70 30 100                                                                              100 100              Wild mustard                                                                             75 20 100                                                                              50                                                                              80                                                                              0                                                     Wild oat   70 50 70 0 30                                                                              0 30 70 70                                                                              80 80 60 80 50                                                                              30 40 90 80  70               Wild radish                                                                              30 0                                                               __________________________________________________________________________

What is claimed is:
 1. A compound of the formula ##STR26## wherein R isC₁ -C₄ alkyl, CH₂ CH=CH₂, CH₂ C{CH, cyclopropylmethyl or CH₂ CH₂ R_(2;)R₁ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, CH₂ CN, CH₂ CH₃, C₁ -C₃ alkoxy, C₁-C₃ alkylthio, phenylthio or NR₃ R₄ ; R₂ is C₁ -C₂ alkoxy, C₁ -C₂alkylthio, CN or halogen; R₃ and R₄ are independently H or CH₃ ; and Xis NHCH₃, N(CH₃)₂ or N(CH₃)OCH₃ ; provided that when R₁ is OCH₂ CH₃ orCH₂ OCH3, then R is other than CH3;and their agriculturally suitablesalts.
 2. The compounds of claim 1 whereinR is C₁ -C₄ alkyl; R₁ is C₁-C₂ alkyl; and X is NHCH₃ or N(CH₃)₂.
 3. The compounds of claim 1whereinR is C₁ -C₄ alkyl; R₁ is C₁ -C₂ haloalkyl; and X is NHCH₃ orN(CH₃)₂.
 4. The compounds of claim 2 whereinR is C₁ -C₃ alkyl; and X isNHCH₃)₂.
 5. The compounds of claim 2 whereinR is C₁ -C₃ alkyl; and X isN(CH₃)₂.
 6. A compound of claim 1 which isethyl2-[[[[[4-(dimethylamino-6-(2,2,2-trifluoroethoxy)-3,5-triazin-2-yl]amino]carbonyl]amino]-sulfonyl]-3-methylbenzoate.
 7. A compound of claim 1 which ismethyl2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethyoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]-sulfonyl]-3-methylbenzoate.8. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 1and at least one of the following: surfactant, solid diluent or liquiddiluent.
 9. A composition suitable for controlling the growth ofundesired vegetation which comprises an effective amount of a compoundof claim 2 and at least one of the following: surfactant, solid diluentor liquid diluent.
 10. A composition suitable for controlling the growthof undesired vegetation which comprises an effective amount of acompound of claim 3 and at least one of the following: surfactant, soliddiluent or liquid diluent.
 11. A composition suitable for controllingthe growth of undesired vegetation which comprises an effective amountof a compound of claim 4 and at least one of the following: surfactant,solid diluent or liquid diluent.
 12. A composition suitable forcontrolling the growth of undesired vegetation which comprises aneffective amount of a compound of claim 5 and at least one of thefollowing: surfactant, solid diluent or liquid diluent.
 13. Acomposition suitable for controlling the growth of undesired vegetationwhich comprises an effective amount of a compound of claim 6 and atleast one of the following: surfactant, solid diluent or liquid diluent.14. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 7and at least one of the following: surfactant, solid diluent or liquiddiluent.
 15. A method for the control of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 16. A method for the control of undesiredvegetation which comprises applying to the locus to be protected aneffective amount of a compound of claim
 2. 17. A method for the controlof undesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 3. 18. A method forthe control of undesired vegetation which comprises applying to thelocus to be protected an effective amount of a compound of claim
 4. 19.A method for the control of undesired vegetation which comprisesapplying to the locus to be protected an effective amount of a compoundof claim
 5. 20. A method for the control of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 6. 21. A method for the control of undesiredvegetation which comprises applying to the locus to be protected aneffective amount of a compound of claim
 7. 22. The method of claim 20wherein the locus to be protected is a sugar beet crop.
 23. The methodof claim 21 wherein the locus to be protected is a sugar beet crop.